Vacation rentals in Winona Lakes

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Top-rated vacation rentals in Winona Lakes

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Chalet in East Stroudsburg
4.78 out of 5 average rating, 430 reviews

BLVCK Cabin I w/ wood Hot Tub near Bushkill Falls

Escape to the designer Black Cabin near Bushkill Falls—your perfect mountain getaway. Surrounded by forest and within walking distance to peaceful creek access for kayaking or fishing, this stylish all black retreat sleeps 6 with two queen bedrooms &a cozy loft. Enjoy the open kitchen with high-end appliances, a warm pellet stove & wraparound deck with gas firepit and outdoor TV. Relax in the wood-fired hot tub or by the firepit under the stars. Only 20 min to Shawnee Mountain & Bushkill Falls.

Guest favorite
The A-frame chalet is surrounded by lush greenery, featuring a welcoming front porch with steps leading to the entryway. Large windows allow ample natural light to fill the interior. A small shed is visible in the background, accentuating the tranquil forest setting.
Cabin in East Stroudsburg
4.97 out of 5 average rating, 152 reviews

Norway Chalet: Forest Escape

Located Conveniently in the Pocono's, just 1 hour 30 minutes from Manhattan and under 2 hours from Philly! Our relaxing A-Frame Chalet is inspired by European design/ architecture and gives you the feel of a Nordic Home in the Poconos. Enjoy 4 large decks where you can hear the birds chirping and watch humming birds, butterflies, deer, and other wildlife in a "jungle like" back yard. Just minutes from the most popular hiking destinations, and water falls. Pets are welcome free of charge (:

Guest favorite
A spacious living and dining area features a blend of comfortable furniture, including a green armchair and a sleek table with chairs. A small decorative rug lies on the tiled floor, and a television is mounted on the wall. Natural light enters through a window, accentuating the room's warmth.
Guest suite in Hackettstown
4.88 out of 5 average rating, 143 reviews

Full Apartment near Hackettstown

Enjoy this private apartment connected to an 18th century stone house. It comes furnished with 1 1/2 bathrooms, a fully equipped kitchen, large living/dining room, and one bedroom with closet and a queen sized bed. We are located in the beautiful highlands of northwest NJ--about 60 miles from Lincoln Tunnel and 75 miles from Philadelphia. Nearby are historical sights, great hiking and skiing areas restaurants, brew pubs, and a train station. Private parking provided next to entrance.

Top guest favorite
A castle-style retreat is showcased, featuring a whimsical dragon statue and a large chess set in the foreground. A tranquil pond with a fountain is visible, alongside a magnificent castle structure designed with classic stone elements and a welcoming entrance, all set amidst lush greenery.
Castle in East Stroudsburg
4.99 out of 5 average rating, 412 reviews

Pocono Castle w/ Dungeon Escape Room &Private Pond

Sleep in a Fairy Tale at Pocono Castle! Live the dream in this 2,300 sq. ft storybook retreat, where you’ll sleep like royalty in a real fairy tale castle. Unwind in luxury with a bubbling hot tub, a cedar sauna, and endless magical touches. Dress up as Kings, Queens, or Knights and explore the grounds, featuring a private one-acre pond & maybe you’ll catch a Golden Fish! With enchanting bedrooms, outdoor adventures, and unforgettable charm, this is the OMG getaway you’ve been waiting for!

Top guest favorite
Guest suite in Columbia
5 out of 5 average rating, 291 reviews

DWG Mountain Oasis-Private Apt w/Frog Pond

Private family apartment built for relaxing comfort and views of nature 2 miles from Mount Tammany, Mount Minsi, and the Appalachian Trail Walk to a private brookside trail and a winery Private deck Includes: Bread, eggs, pancake mix, coffee, tea, milk, bananas, s'mores kit, and more AWARDS: Top 1% of all Airbnb & #1 "Most Hospitable NJ Host" in 2021 Little or no host interaction – your choice Host lives on-site and can provide customized recommendations for food and things to do

Top guest favorite
A cozy living area features warm wooden paneling and a plush sofa with light-colored cushions. A wooden coffee table holds two water bottles and a binder, while a stone fireplace adds character. Natural light streams in through large windows, enhancing the inviting atmosphere.
Farm stay in Cresco
4.96 out of 5 average rating, 176 reviews

The Thoroughbred Cottage at Pleasant Ridge Farm

The Thoroughbred Cottage is the quintessential, early 1900s Pocono vacation cottage. Located on our commercial horse farm, the cottage has been entirely renovated but has kept its unique original details. Views include our upper pastures and wooded hillside of the state game lands beyond. The cottage is set back on our private lane, but is close to all major Pocono attractions and wedding venues. A perfect, cozy little getaway for couples. Not suitable for infants or children

Top guest favorite
A well-organized bedroom features a queen bed dressed in a patterned coverlet with animal motifs. Two nightstands with lamps flank the bed. Natural light enters through the large window, complemented by white blinds. A door and wall decor add warmth to the inviting space.
Guesthouse in East Stroudsburg
4.96 out of 5 average rating, 163 reviews

Cassie's Cozy Cottage- Poconos Near Shawnee

Welcome to Cassie's Cozy Cottage! Enjoy a peaceful stay suited for two people. Located near various outdoor recreational activities like skiing/snowboarding, hiking trails, river activities, golf courses, and also shopping outlets. Shawnee Mountain-3.7 miles, Camelback Mountain-12 miles, Delaware River Access- (Smithfield beach) 4.6 miles (Bushkill Access) 14 miles, Bushkill Falls- 10 miles. The Crossings Premium Outlets- 10 miles, ...and many more areas to visit close by.

Top guest favorite
The living area showcases a spacious layout with hardwood floors and large windows allowing natural light to flood the space. A black sofa is positioned near the double-height ceiling under a skylight, enhancing the open feel of the room. A staircase leads to additional areas.
Home in East Stroudsburg
4.84 out of 5 average rating, 218 reviews

Quiet rustic house/Jacuzzi in safe gated community

"Enjoy this beautiful spacious home that is located in a secured gated community, Indoor jacuzzi tub in the master bedroom on the second floor , the jacuzzi is a lay down tub for 2 people max .There is free parking on the premises, the driveway can hold up to 5 vehicles. The home is equipped with fast high speed WiFi that can be access all around the home." I have air conditioners in the top 2 floor bedrooms, the house stays cool in summer as well

Superhost
A cozy dining area features a wooden table with a checkered tablecloth and two chairs. Decorative items, including a flower arrangement and wall art, enhance the warm ambiance. Large windows allow natural light to brighten the space, creating a welcoming atmosphere.
Farm stay in Saylorsburg
4.94 out of 5 average rating, 243 reviews

Adorable Farm Cottage

This memorable place is anything but ordinary. The cottage is located on an organic farm. We have a staff onsite that is always buzzing around and happy to help you answer any questions you may have. We have a Wood Fire brick oven bakery on site as well. This is not just any Farm anyone who visits will understand the love that surrounds us! This cottage is not just a place to stay but an AMAZING experience as well!

Guest favorite
Cottage in East Stroudsburg
4.98 out of 5 average rating, 211 reviews

Serene Poconos Cottage • Peaceful Retreat

Escape to Woodland Serenity at “The Cottage in the Woods”. This peaceful, private retreat is perfect for remote work with fast WiFi and a sun-filled four-season room. Ideal for monthly furnished stays—whether relocating, house-hunting, or renovating nearby. A highly sought-after monthly summer vacation rental, loved for its tranquility, deer sightings, and relaxing evenings by the fire pit in the Pocono Mountains.

Top guest favorite
The exterior of the rustic cottage features a wooden facade and two sets of French doors. Chairs are positioned on a stone path leading to the entrance, surrounded by a manicured garden area with pebbles and greenery. Nearby trees provide a natural backdrop.
Guesthouse in Stroudsburg
4.95 out of 5 average rating, 227 reviews

Cozy guest cottage with indoor fireplace

Take it easy at this unique getaway in the Poconos! This vintage one room cottage is the perfect space for soaking in nature, getting creative, or exploring the attractions of the Pocono Mountains. The cozy cottage is within 20 minutes of ski resorts, Kalahari, and the Delaware Water Gap national recreation park. Reach downtown Stroudsburg and it’s restaurants and nightlife within 7 minutes.

Guest favorite
A wooden dining table is surrounded by three chairs and a bench, set against a backdrop of large sliding doors leading to a deck. Natural light filters in through sheer white curtains, highlighting the tree views outside. Framed art decorates the wall beside a window.
Cabin in East Stroudsburg
4.92 out of 5 average rating, 132 reviews

Nature serene Cabin near popular hiking/waterfalls

Your trailhead starts here. Experience a unique stay surrounded by nature and sunset serenity. Thoughtfully remodeled and furnished for coziness and comfort in mind, this place is perfect for gatherings with family and friends, or a mere relaxing stay with a partner. The highlight of this place is the sunroom, accompanied by an entertainment room, providing the essentials for your enjoyment.

Popular amenities for Winona Lakes vacation rentals